Isolation and biosynthesis of daturamycins from Streptomyces sp. KIB-H1544

• Yin Chen,
• Jinqiu Ren,
• Ruimin Yang,
• Jie Li,
• Sheng-Xiong Huang and
• Yijun Yan

Beilstein J. Org. Chem. 2022, 18, 1009–1016, doi:10.3762/bjoc.18.101

• skeleton exhibit a large number of structural diversity due to the differences of the center ring and the connection among rings. Structurally, most natural terphenyls are p-terphenyl derivatives consisting of a C-18 tricyclic or polycyclic C-18 aromatic skeleton. Diarylcyclopentenones, which possess a

Molecular diversity of the base-promoted reaction of phenacylmalononitriles with dialkyl but-2-ynedioates

• Hui Zheng,
• Ying Han,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2022, 18, 991–998, doi:10.3762/bjoc.18.99

• ][4][5], because it contains one carbonyl group, two cyano groups, and an activated methylene unit. Phenacylmalononitrile exhibits versatile reactivity, high synthetic efficiency and molecular diversity and has been widely employed in many synthetic reactions [6][7][8][9][10]. On the other hand

Morita–Baylis–Hillman reaction of 3-formyl-9H-pyrido[3,4-b]indoles and fluorescence studies of the products

• Nisha Devi and
• Virender Singh

Beilstein J. Org. Chem. 2022, 18, 926–934, doi:10.3762/bjoc.18.92

• family and is associated with a broad spectrum of biological properties. 3-Formyl-9H-pyrido[3,4-b]indole is a such potent precursor belonging to this family which can be tailored for installing diversity at various positions of β-carboline to generate unique molecular hybrids of biological importance

• reaction has gained considerable attention from the past two decades as these MBH adducts are highly functionalized and offer various points of diversity. Due to these amazing features, these MBH adducts act as starting material on which various organic transformations can be performed leading to the

• –Spengler (P-S) or Bischler–Napieralski (B-N) cyclisation, introduction of a formyl group at C-1 or C-3 position of the β-carboline frameworks may provide a new route for generating unlimited diversity at C-1 as well as at the C-3 position of β-carbolines. As depicted in Figure 2, 1-formyl-β-carbolines and

Anti-inflammatory aromadendrane- and cadinane-type sesquiterpenoids from the South China Sea sponge Acanthella cavernosa

• Shou-Mao Shen,
• Qing Yang,
• Yi Zang,
• Jia Li,
• Xueting Liu and
• Yue-Wei Guo

Beilstein J. Org. Chem. 2022, 18, 916–925, doi:10.3762/bjoc.18.91

• diterpenes with characteristic isocyano, isothiocyano, and formamido functionalities [2][3][4][5]. Many of these secondary metabolites merit further investigation due to their intriguing structural diversity and wide spectra of biological activities ranging from antifeedant, antifouling, and cytotoxic to

• sesquiterpenoids not only extended the members of the sesquiterpenoid family but also enriched the chemical diversity of the Acanthella sponges. The plausible biosynthetic pathway of isolated compounds 1–7 was also proposed. Up to date, no sesquiterpene cyclase has been characterized for aromadendrane and

Efficient production of clerodane and ent-kaurane diterpenes through truncated artificial pathways in Escherichia coli

• Fang-Ru Li,
• Xiaoxu Lin,
• Qian Yang,
• Ning-Hua Tan and
• Liao-Bin Dong

Beilstein J. Org. Chem. 2022, 18, 881–888, doi:10.3762/bjoc.18.89

• ), have attracted great attention from chemists and biologists due to their intriguing chemical structures and broad pharmacological functions [1][2][3][4]. The vast structural diversity of diterpenoids arise biosynthetically from the following two stages: i) diterpene synthase (DTS, also called diterpene

• skeletons resulting in a large array of oxidative diversity [5][6][7]. Nature’s ability to efficiently biosynthesize diterpenoids has attracted chemists to mimic it for the synthesis of complex diterpenoids using either pure chemical tools, exemplified by the ‘two-phase strategy’ pioneered by the Baran

Copper-catalyzed multicomponent reactions for the efficient synthesis of diverse spirotetrahydrocarbazoles

• Shao-Cong Zhan,
• Ren-Jie Fang,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2022, 18, 796–808, doi:10.3762/bjoc.18.80

• with two molecules of 2-methylindole under the same reaction conditions to generate the well-known 3,3'-(p-tolylmethylene)bis(2-methylindole) (6a) in 75% yield. Subsequently, we sought to determine the generality of aromatic aldehydes. As illustrated in Scheme 6, a diversity of functional groups, which

Synthesis of odorants in flow and their applications in perfumery

• Merlin Kleoff,
• Paul Kiler and
• Philipp Heretsch

Beilstein J. Org. Chem. 2022, 18, 754–768, doi:10.3762/bjoc.18.76

• Originally, musk was obtained from the gland of the musk deer and used as a powerful base note. Due to the high price of musks of natural origin, the vast majority of them is produced by chemical synthesis. Today, a plethora of synthetic musks with a broad structural and olfactory diversity are available

Identification of the new prenyltransferase Ubi-297 from marine bacteria and elucidation of its substrate specificity

• Jamshid Amiri Moghaddam,
• Huijuan Guo,
• Karsten Willing,
• Thomas Wichard and
• Christine Beemelmanns

Beilstein J. Org. Chem. 2022, 18, 722–731, doi:10.3762/bjoc.18.72

• farnesylation of quinoline derivatives, such as 8-hydroxyquinoline-2-carboxylic acid (8-HQA) and quinaldic acid. The results of this study provide new insights into the abundance and diversity of Ptases in marine Flavobacteria and beyond. Keywords: Flavobacteria; prenylation; Saccharomonospora; UbiA-like

• biosynthetic repertoire of marine bacteria [14][15], the diversity of the encoded and yet often unexplored bacterial Ptases of Flavobacteria and Saccharomonospora strains sparked our interest. In this study we investigated three yet poorly described homologous Ptases within the UbiA superfamily and evaluated

• , we aimed to gain insights into abundance and diversity of Ptases encoded in both, Flavobacteria and members of the Phylum Actinobacteria, as these were suggested to be involved in the production of meroterpenoids [2]. Thus, the genomes of marine Flavobacteria, including members of the genera

Structural basis for endoperoxide-forming oxygenases

• Takahiro Mori and
• Ikuro Abe

Beilstein J. Org. Chem. 2022, 18, 707–721, doi:10.3762/bjoc.18.71

• , natural and (semi)synthetic endoperoxides with wide structural diversity show antimalarial activity against Plasmodium falciparum malaria. In this case, the reductive activation of the endoperoxide ring with the homolytic cleavage of the O–O bond leads to the generation of carbon-centered free radicals

Tri(n-butyl)phosphine-promoted domino reaction for the efficient construction of spiro[cyclohexane-1,3'-indolines] and spiro[indoline-3,2'-furan-3',3''-indolines]

• Hui Zheng,
• Ying Han,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2022, 18, 669–679, doi:10.3762/bjoc.18.68

• advantages of using readily available substrates, simple operation, good yields, and molecular diversity, which enable it to find potential applications in heterocyclic and medicinal chemistry. Experimental 1. General procedure for the preparation of the spiro[cyclohexane-1,3'-indolines] 3a–w: In an

Heteroleptic metallosupramolecular aggregates/complexation for supramolecular catalysis

• Prodip Howlader and
• Michael Schmittel

Beilstein J. Org. Chem. 2022, 18, 597–630, doi:10.3762/bjoc.18.62

• . Since most of the current metallosupramolecular catalytic systems are homoleptic in nature, the idea of breaking/reducing symmetry has ignited a vivid search for heteroleptic aggregates that are made up by different components. Their higher degree of functional diversity and structural heterogeneity

• ][20][21][22], the idea of breaking/reducing symmetry has ignited a vivid search for heteroleptic aggregates that are made up by different components. Their higher degree of functional diversity and structural heterogeneity should allow, as amply demonstrated by Nature, for instance, by the

A study of the photochemical behavior of terarylenes containing allomaltol and pyrazole fragments

• Constantine V. Milyutin,
• Andrey N. Komogortsev,
• Boris V. Lichitsky and
• Valeriya G. Melekhina

Beilstein J. Org. Chem. 2022, 18, 588–596, doi:10.3762/bjoc.18.61

• two stages: 6π-electrocyclization of 1,3,5-hexatriene systems and subsequent aromatization of the central benzene ring. Among the significant diversity of terarylenes, compounds containing a 5-hydroxy-2-methyl-4H-pyran-4-one (allomaltol) fragment are of particular interest. For such systems two types

Bioinspired tetraamino-bisthiourea chiral macrocycles in catalyzing decarboxylative Mannich reactions

• Hao Guo,
• Yu-Fei Ao,
• De-Xian Wang and
• Qi-Qiang Wang

Beilstein J. Org. Chem. 2022, 18, 486–496, doi:10.3762/bjoc.18.51

• % yields. It is worth noting that common dilute conditions for macrocyclization reactions was not required here. Due to the very high efficiency, gram-scale preparation of the chiral macrocycles was readily achieved (see Supporting Information File 1). To enrich the diversity of the macrocyclic scaffolds

• fragment-coupling approach, different chiral diamine units, including the homo- and hetero-combination, can be easily incorporated. This provides a very rich structural diversity of the macrocycles and allows for fine tuning of the chiral cavity environments. With the short and high-yielding synthesis

• contrast, reactions catalyzed by acyclic analogues containing very similar structural units were non-selective, suggesting the essential role of the rigid macrocyclic framework in realizing efficient stereocontrol. With the easy synthesis, rich structural diversity, cooperative binding and activation sites

Tosylhydrazine-promoted self-conjugate reduction–Michael/aldol reaction of 3-phenacylideneoxindoles towards dispirocyclopentanebisoxindole derivatives

• Sayan Pramanik and
• Chhanda Mukhopadhyay

Beilstein J. Org. Chem. 2022, 18, 469–478, doi:10.3762/bjoc.18.49

• derivatives were synthesized on the basis of Michael acceptor ability of 3-alkylidene oxindoles with various donor synthons [16][17][18][19][20][21][22]. However, in spite of the progress in the synthesis of dispirocyclopentanebisoxindoles with concise structural and stereochemical diversity, the one-pot

Regioselectivity of the S_EAr-based cyclizations and S_EAr-terminated annulations of 3,5-unsubstituted, 4-substituted indoles

• Jonali Das and
• Sajal Kumar Das

Beilstein J. Org. Chem. 2022, 18, 293–302, doi:10.3762/bjoc.18.33

• constructing carbon–carbon and carbon–heteroatom bonds in organic synthesis [8][9][10]. In the course of their diversity-oriented synthesis of indole-based peri-annulated compounds, You and co-workers in 2013 reported the intramolecular Tsuji–Trost reaction of indolyl allyl carbonates 1 under the catalysis of

New advances in asymmetric organocatalysis

• Radovan Šebesta

Beilstein J. Org. Chem. 2022, 18, 240–242, doi:10.3762/bjoc.18.28

• organocatalysis edited by one of the pioneers Benjamin List. After another decade, this thematic issue likes to survey new advances in this field. Three review articles and nine research papers showcase the diversity and breadth into which asymmetric organocatalysis has grown since then. The suitability of

Anomeric 1,2,3-triazole-linked sialic acid derivatives show selective inhibition towards a bacterial neuraminidase over a trypanosome trans-sialidase

• Peterson de Andrade,
• Sanaz Ahmadipour and
• Robert A. Field

Beilstein J. Org. Chem. 2022, 18, 208–216, doi:10.3762/bjoc.18.24

• differences in sialidases that need to be addressed in order to achieve selective inhibition. Keywords: inhibition; neuraminidase; sialic acid; trans-sialidase; 1,2,3-triazole; Introduction Amongst the diversity of glycans present in living organisms, N-acetylneuraminic acid (Neu5Ac, sialic acid) is

Glycosylated coumarins, flavonoids, lignans and phenylpropanoids from Wikstroemia nutans and their biological activities

• Meifang Wu,
• Xiangdong Su,
• Yichuang Wu,
• Yuanjing Luo,
• Ying Guo and
• Yongbo Xue

Beilstein J. Org. Chem. 2022, 18, 200–207, doi:10.3762/bjoc.18.23

• diversity of the secondary metabolites from the genus Wikstroemia. Keywords: coumarin glucosides; flavonoids; lignans; structure elucidation; Wikstroemia nutans; Introduction The genus Wikstroemia (Thymelaeaceae) contains approximately 62 species, which are widespread throughout the subtropical regions of

• antimicrobial activities. This is the first report of the isolation of coumarins, flavonoids, lignans and phenylpropanoid glycosides from W. nutans, while compounds 1–3, 8, and 11 was encountered from the genus Wikstroemia for the first time. Our work will enrich the chemistry and structure diversity of natural

Green synthesis of C5–C6-unsubstituted 1,4-DHP scaffolds using an efficient Ni–chitosan nanocatalyst under ultrasonic conditions

• Soumyadip Basu,
• Sauvik Chatterjee,
• Suman Ray,
• Suvendu Maity,
• Prasanta Ghosh,
• Asim Bhaumik and
• Chhanda Mukhopadhyay

Beilstein J. Org. Chem. 2022, 18, 133–142, doi:10.3762/bjoc.18.14

• . We mainly focused on the synthesis under green aspects and towards a high product diversity. We initially chose three green solvents with a relatively low boiling point, ethanol, water, and acetone, respectively, as a reaction medium. A series of reactions was examined in these solvents, using an

Tenacibactins K–M, cytotoxic siderophores from a coral-associated gliding bacterium of the genus Tenacibaculum

• Yasuhiro Igarashi,
• Yiwei Ge,
• Tao Zhou,
• Amit Raj Sharma,
• Enjuro Harunari,
• Naoya Oku and
• Agus Trianto

Beilstein J. Org. Chem. 2022, 18, 110–119, doi:10.3762/bjoc.18.12

• from 2.5 to 7.9 Mbp, biosynthetic gene clusters for siderophores, terpenes, and non-ribosomal peptides were identified by genome mining [39], suggesting a high capability of secondary metabolism in this genus. Further investigation is underway to disclose the actual diversity of metabolites from the

Earth-abundant 3d transition metals on the rise in catalysis

• Nikolaos Kaplaneris and
• Lutz Ackermann

Beilstein J. Org. Chem. 2022, 18, 86–88, doi:10.3762/bjoc.18.8

• the editor of this issue on Earth-abundant 3d metal catalysis, it was a wonderful experience to experience the diversity of 3d transition metal catalysis, which continues to address key challenges of sustainable modern molecular syntheses. The senior author owe a great debt of gratitude to all of the

Peptide stapling by late-stage Suzuki–Miyaura cross-coupling

• Hendrik Gruß,
• Rebecca C. Feiner,
• Ridhiwan Mseya,
• David C. Schröder,
• Michał Jewgiński,
• Kristian M. Müller,
• Rafał Latajka,
• Antoine Marion and
• Norbert Sewald

Beilstein J. Org. Chem. 2022, 18, 1–12, doi:10.3762/bjoc.18.1

• , analysis of the structural diversity of the two isomers of P5 indicates that P5 cis (P5.1) is more disordered (see Supporting Information File 1, Table S3), which also correlates with a blue-shifted absorption minimum compared to P5 trans (P5.2). In the partially helical structures of aAxWt (i.e., second

• would be speculative to link this property of the P5 to its enhanced biological activity. Instead, we find a more likely reason for the greater activity of P5.2 over that of aAxWt in analysing the conformational diversity of the two peptides (see Supporting Information File 1, Table S2). In P5 trans

A photochemical C=C cleavage process: toward access to backbone N-formyl peptides

• Haopei Wang and
• Zachary T. Ball

Beilstein J. Org. Chem. 2021, 17, 2932–2938, doi:10.3762/bjoc.17.202

• then account for the isolation of the acetylated analogue 9. The photochemical pathway described here represents a formal oxidative olefin cleavage of vinylogous nitroaryl-modified amides and ethers. The pathway adds to the diversity of photochemical pathways known for 2-nitrophenyl systems, and the

Selective sulfonylation and isonitrilation of para-quinone methides employing TosMIC as a source of sulfonyl group or isonitrile group

• Chuanhua Qu,
• Run Huang,
• Yong Li,
• Tong Liu,
• Yuan Chen and
• Guiting Song

Beilstein J. Org. Chem. 2021, 17, 2822–2831, doi:10.3762/bjoc.17.193

• preparation of highly valuable diarylmethyl sulfones are relatively scarce [24]. In addition, the important link between structural diversity and complexity with bioactivity represented by sulfones has led to the goal of developing strategies to as many these pivotal scaffolds as possible. Isocyanide is an

Me₃Al-mediated domino nucleophilic addition/intramolecular cyclisation of 2-(2-oxo-2-phenylethyl)benzonitriles with amines; a convenient approach for the synthesis of substituted 1-aminoisoquinolines

• Krishna M. S. Adusumalli,
• Lakshmi N. S. Konidena,
• Hima B. Gandham,
• Krishnaiah Kumari,
• Krishna R. Valluru,
• Satya K. R. Nidasanametla,
• Venkateswara R. Battula and
• Hari K. Namballa

Beilstein J. Org. Chem. 2021, 17, 2765–2772, doi:10.3762/bjoc.17.186

• of aza-heterocycles with unparalleled structural diversity, and is considered to be associated with a huge range of applications in medicinal and materials sciences [5][6][7][8][9][10][11][12]. 1-Amino substituted isoquinoline derivatives are extensively studied owing to their therapeutic